Orthooxyazo dye



ll atented @et l0, W229 111 ll" lTiid WILHELM HERZBERG, OFBERLIN-'WILMERSDORF, AND OSWALD SGHARFENBERG', 01E BERLIN-SGHONEBERG,GERMANY} ASfiIGINORS 'lO ACTJEEN GESJELLSGHAFT FUR ANILIN FABRIKATIOIN,OF BERLIN, GERZMANY.

OETHOOIIYAZO DYE.

No Drawing.

T 0 all whom it may concern Be it known that we, WILHELM Hnnznnne andOswALI) SOHARFENBERG, citizens of the German Republic, residing atBerlinWVilmersdorif, Germany, and Berlin-Schoneberg, Germany, our P. 0.address being Prinzregentenstr. 10, Berlin-Wilmersdorf, Germany, andltosenheimerstr. 12, Berlin- Schoneberg, Germany, have invented certainnew and useful Improvements in Orthooxyazo Dyes (for which we have filedapplications in Germany August 28, 1917 Germany, January 18, 1918;Germany, April 22, 1918; England, June 8, 1920; France, June 19, 1920;Italy, June 7, 1920; Switzerland, July 8, 1920; Czecho-Slovakia, June17, 1920), of which the following is a specification.

By our invention by combining a diazotised 2-aminophenol derivativewhich contains negative radicals such as halogen with8-halogen-1-oXynaphthalene-5-sulfonic acid new valuable dyestuiis forwool are produced their chromium lakes having a very good fastness. Theyform in the dry pulverised shape dark powders soluble in water to bluesolutions being insoluble in alcohol, ether, benzene, yielding uponreduction S- chloro-2-amino-1-oXynaphthalene5-sulfonic acid and a2-aminophenol derivative, dyeing on wool with chromium mordants bluetints oi? a very good fastness.

The 2-aminophenol derivatives containing a i'iegative rad icle such ashalogen which may be employed are represented by the general formula inwhich X stands for univalent substituents such as hydrogen, alkyl orhalogen and at least one of these substituents is a negative group suchas halogen.

The following example illustrates our invention, the parts being byweight:

21 parts of 2-amino-3. 1.5--t1,"ichlorophenol Serial No. 4496,9 70.-

are diazotised in the usual manner. The diazo compound is allowed to runinto a solution of 25.9 parts of 8 chloro-1-o1 ynaphthalene-5-sulfonicacid, alkaline with sodium carbonate. The dyestufl is separated andworked up as usual. It dyes wool with chromium mordants clear bluetints.

It is obvious to those skilled in the art that our invention is notlimited to the foregoing example or to the details given therein.Similar dyes may be'obtained by substituting for the parent material inthe foregoing example other compounds within the foregoing definition.

WV hat we claim is, p

1. The herein described new ortho-oXy-azo dyes being in the shape ofalkali metal salts dark powders soluble in water to blue solutions fromwhich an inorganic or organic acid separates a brownish orangeprecipitation, the aqueous solution becoming violet by addition ofsodium carbonate, red by addition of sodium hydroxide, yielding upon reduction 8-chloro-2-amino-1-oxynaphthalene- 5-sulfonic acid and2-amino-3.L5-trihalogenated l-oxybenzene, dyeing on wool with chromiummordants blue tints of a very good fastness and corresponding as freeacids to the general formula:

separates a brownish orange precipitation,

the aqueous solution becoming violet by addition of sodium carbonate,red by addition of sodium hydroxide, yielding upon re duction8-chloro-2-amino-1-oxynaphthalene- 5-suli onic acid and 2-amino-3.4e.5trichloro-1- oxybenzene, dyeing 011 wool wlth chromium mordants clearblue tints of a very good In testimony whereof we, :Lflix 0msignn- '10tures 1n presence of two \vltnosses.

\VILHELM HERZBERG. OSWA LI) SUITA'R FEN B F/l-H 1'.

Witnesses Dr. GERI-IARD Home, Dr. RUDOLF I'IAUGWITZ.

